合成路线:The reaction of methyl 9alpha,11alpha,15(S)-trihydroxy-17(S),20-dimethylprosta-5(Z),13(E)-dienoate (I) with I2 and NaHCO3 in water dichloromethane gives the iodoepoxy compound (II),which is treated with dihydropyran-p-toluenesulfonic acid in dichloromethane to protect the hydroxyl groups yielding the bistetrahydropyranyl derivative (II).The dehydrohalogenation of (III) with 1,5-diazabicyclo[5.4.O]-5-undecene (DBU) followed by hydrolysis with HCl affords the hydroxyketone (IV),which is further oxidized with CrO3-MnSO4-H2SO4 to the diketone (V).Finally,this compound is deprotected with aqueous acetic acid in THF.
参考文献标题:Ornoprostil
文献作者:Castar,R.M.; Serradell,M.N.; Castar,J.
参考来源:Drugs Fut 1987,12(11),1023
合成路线:The reaction of methyl 9alpha,11alpha,15(S)-trihydroxy-17(S),20-dimethylprosta-5(Z),13(E)-dienoate (I) with I2 and NaHCO3 in water dichloromethane gives the iodoepoxy compound (II),which is treated with dihydropyran-p-toluenesulfonic acid in dichloromethane to protect the hydroxyl groups yielding the bistetrahydropyranyl derivative (II).The dehydrohalogenation of (III) with 1,5-diazabicyclo[5.4.O]-5-undecene (DBU) followed by hydrolysis with HCl affords the hydroxyketone (IV),which is further oxidized with CrO3-MnSO4-H2SO4 to the diketone (V).Finally,this compound is deprotected with aqueous acetic acid in THF.
参考文献标题:
文献作者:Suarez-Kurtz,G.; et al.
参考来源:Res Disclosure 1985,256(9),400-401
产品链接: CAS No. 70667-26-4››